EP0240918A1 - Oxonitriles diphosphonylés, procédé de leur préparation et leur utilisation en compositions microbistatiques et compositions microbistatiques contenant des oxonitriles diphosphonylés - Google Patents
Oxonitriles diphosphonylés, procédé de leur préparation et leur utilisation en compositions microbistatiques et compositions microbistatiques contenant des oxonitriles diphosphonylés Download PDFInfo
- Publication number
- EP0240918A1 EP0240918A1 EP87104805A EP87104805A EP0240918A1 EP 0240918 A1 EP0240918 A1 EP 0240918A1 EP 87104805 A EP87104805 A EP 87104805A EP 87104805 A EP87104805 A EP 87104805A EP 0240918 A1 EP0240918 A1 EP 0240918A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- general formula
- iii
- compounds
- water
- cation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 20
- 239000011574 phosphorus Substances 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 9
- 239000012050 conventional carrier Substances 0.000 claims abstract description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 9
- 150000007513 acids Chemical class 0.000 claims abstract description 8
- 150000001768 cations Chemical class 0.000 claims abstract description 7
- 239000011541 reaction mixture Substances 0.000 claims abstract description 7
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 6
- 239000013543 active substance Substances 0.000 claims abstract description 4
- 229910052794 bromium Chemical group 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 13
- -1 alkali metal cation Chemical class 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- 238000005954 phosphonylation reaction Methods 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910001415 sodium ion Inorganic materials 0.000 claims description 3
- XGIAHMUOCFHQTI-UHFFFAOYSA-N Cl.Cl.Cl.Cl.CC Chemical compound Cl.Cl.Cl.Cl.CC XGIAHMUOCFHQTI-UHFFFAOYSA-N 0.000 claims description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000000460 chlorine Chemical group 0.000 abstract description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 244000052616 bacterial pathogen Species 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 241000194019 Streptococcus mutans Species 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000008139 complexing agent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 150000003009 phosphonic acids Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- ILZVLLNQIKWNDM-UHFFFAOYSA-N (1-amino-4,4-dimethyl-3-oxo-1-phosphonodecyl)phosphonic acid Chemical compound CCCCCCC(C)(C)C(=O)CC(N)(P(O)(O)=O)P(O)(O)=O ILZVLLNQIKWNDM-UHFFFAOYSA-N 0.000 description 1
- VPPUBTQWISEIRH-UHFFFAOYSA-N 4,4-dimethyl-3-oxodecanenitrile Chemical compound CCCCCCC(C)(C)C(=O)CC#N VPPUBTQWISEIRH-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 229910020667 PBr3 Inorganic materials 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3839—Polyphosphonic acids
- C07F9/3873—Polyphosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
Definitions
- the invention relates to through Diphosphonyltechnik O xonitrilen available 3-alkyl-3-oxo-1-aminopropane 1.1-diphosphonic acids--its water-soluble salts, processes for their preparation and their use in microbistatic compositions as well as the microbistatic effective, the diphosphonyl possess said derivatives containing compositions and .
- 1-amino-1,1-diphosphonic acids of the following general formula (I) in which A, B and C represent aliphatic, cycloaliphatic or aromatic hydrocarbon radicals and B and C can additionally also represent an H atom are known from the prior art. you will be by reacting nitriles with phosphorus trihalides and subsequent hydrolysis or alcoholysis (DE-AS 10 02 355), reacting nitriles with phosphorous acid (DE-OS 26 25 767) or reacting carboxamides with phosphorus trihalides with the addition of phosphorous acid and subsequent hydrolysis ( DE-OS 19 58 123).
- Phosphonic acids of the general formula (I) mentioned above have the ability to complex heavy metal ions and alkaline earth metal ions. They are therefore widely used as complexing agents or chelating agents in water softening, in the production of detergents, in the textile sector or in paper production. DE-AS 10 02 355 also mentions their use in pharmaceuticals and pesticides.
- Structure-related compounds of the general formula (II), which are also known as complexing agents, are also suitable for use in the pharmaceutical field:
- B and C represent hydrogen or aliphatic or aromatic radicals in analogy to the general formula (I) mentioned above, while D represents an alkylene radical having 1 to 5 C atoms.
- DE-PS 24 05 254 and 25 34 391 the use of compounds of general formula (I I ) and their what described in the prophylaxis and the therapeutic treatment of disorders of calcium or phosphate metabolism in the human and animal body.
- the invention relates to 3-alkyl-3-oxo-l-aminopropane-1,1-diphosphonic acids and their water-soluble salts of the general formula (III) in which R represents unbranched or branched alkyl radicals having 1 to 8 carbon atoms, R 2 and R 3 independently of one another represent methyl or ethyl and can be MH or the cation of a water-soluble base.
- the invention also relates to a process for the preparation of the compounds of the general formula (I II ) in which R 1 for unbranched or branched alkyl radicals having 1 to 8 carbon atoms, R 2 and R 3 independently of one another for methyl or ethyl and M for H or the cation of a water-soluble base, which is known is characterized in that - optionally in the presence of one or more organic solvents - at temperatures in the range from 0 to 100 ° C an oxonitrile of the general formula (IV) in which R 1 , R 2 and R 3 can have the meanings given above, either with mixtures of phosphorus trihalides PX 3 'in which X is F, Cl or Br, with phosphorous acid, the molar ratio of the phosphonylation partners in the range from 2: 1 to 1: 2, or with products of the reaction of phosphorus trihalides PX 3 with water, in which the phosphorus trihalide is hydrolyzed to the extent that a PX 3
- reaction products of the general formula (III) in which M is H are then known in a manner known per se by adding basic reactants of the formula M ⁇ OH ⁇ , where M is an alkali metal or ammonium cation
- R 4 R 5 R 6 R 7 N ⁇ is in which R 4 , R 5 , R 6 and R 7 can, independently of one another, be hydrogen or a branched or unbranched alkyl radical having 1 to 12 C atoms, converted into compounds of the formula (III), in which M represents an alkali metal or ammonium cation of the meaning given.
- the compounds of formula (III) obtained are isolated and purified by methods known per se.
- the invention also relates to the use of the compound of the general formula (III) in microbistatically active agents in addition to conventional carriers and auxiliaries.
- the invention further relates to compositions which contain one or more compounds of the general formula (III) with the meanings given above for R 1 , R 2 , R 3 and M in microbistatically active concentrations in addition to conventional carriers and auxiliaries.
- novel compounds of the general formula (III) according to the invention can be referred to as 3-alkyl-3-oxo-1-aminopropane-1,1-diphosphonic acids or their salts .
- R can stand for unbranched or branched alkyl radicals with 1 to 8 carbon atoms.
- Such radicals come from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, tert-butyl, and also n-pentyl, n-hexyl, n-heptyl and n-octyl and their branched ones Isomers in question.
- R - preferably represents unbranched alkyl radicals having 3 to 6 carbon atoms.
- radicals R 2 and R 3 in the general formula (III) given above can be methyl or ethyl independently of one another.
- the two radicals R 2 and R 3 are preferably identical. According to the invention, particular preference is given to compounds (III) in which both R 2 and R 3 are methyl.
- Microbistatically active and thus also the subject of the invention are compounds of the general formula (III) given above, in which M instead of the proton for the free acids can also represent alkali metal cations or an ammonium cation of the general formula R 4 R 5 R 6 R 7 N ⁇ .
- M instead of the proton for the free acids can also represent alkali metal cations or an ammonium cation of the general formula R 4 R 5 R 6 R 7 N ⁇ .
- M represents H. This of course also improves the usability of such compounds in microbistatic agents.
- cations such as N ⁇ or K 8 are particularly suitable as alkali metal cations.
- M can also represent ammonium cations of the general structure above, in which R 4 , R 5 , R 6 and R can independently of one another be hydrogen or branched or unbranched alkyl radicals having 1 to 12 carbon atoms. All branched and unbranched radicals from the group methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl are thus suitable as alkyl radicals.
- alkali metal salts of the general formula (III) in which M stands for an alkali metal cation are preferred as water-soluble salts.
- the sodium salts are particularly preferred.
- PBr 3 is advantageously used as phosphorus trihalide for the process according to the invention.
- a comparable reaction is in the DE-OS 19 58 123.
- a reaction product of phosphorus trihalide with water can also be used if the amounts resulting from the reaction are such that formally a mixture of phosphorus trihalide and phosphoric acid is present, for example in a molar ratio of 1: 1.
- This can be achieved, for example, by using mixtures of phosphorus trihalide, for example phosphorus tribromide, and water in a molar ratio of 2: 3, in which one mole of PX 3 is hydrolyzed to phosphorous acid, while the other is available for the phosphonylation of oxonitrile (III) .
- reaction products of the general formula (III) in which M is H are then optionally converted into their water-soluble salts, preferably their alkali metal salts, by adding basic reactants of the formula M ⁇ OH ⁇ , where M is an alkali metal or ammonium cation, their sodium salts are particularly preferably converted and isolated and purified from the reaction mixture by methods known per se. This can be done, for example, by crystallizing the reaction products dissolved in the reaction mixture at elevated temperature by cooling or precipitating them by adding a solvent, separating the precipitates or crystals obtained from the dissolved reactants by decanting off the mother liquor or by filtration, and separating the precipitates or crystals then dries and optionally further purified by recrystallization.
- compositions which contained one or more compounds of the general formula (III) in concentrations of 0.25 to 1 g / l together with conventional carriers and auxiliaries were particularly effective, with R 3 for one in the general formula (III) straight-chain or branched alkyl radical having 3 to 6 carbon atoms, R 2 and R 3 are methyl and M is an alkali metal cation, preferably a sodium ion.
- compositions are ideally suited to inhibit the growth of numerous gram-positive or gram-negative bacteria even in low concentrations. They have an inhibitory concentration that makes them significantly superior to other comparable microbistatic compositions.
- test tubes An overnight culture was set up from the test germs one day before starting the actual test series. For this purpose, a small amount of bacteria was lifted from a spot of the plate with the inoculation loop densely overgrown with germs and placed in a test tube filled with 10 ml broth. The corresponding test tubes were then incubated at 37 ° C. for 16 to 18 hours and then stored at 4 to 0 ° C. until the test tubes were inoculated.
- the tubes were inoculated with a drop of the corresponding germ suspension.
- As a growth control for all T served estkeime a tube containing 5 ml broth or W RIEF without microbial additive.
- the corresponding test tubes were incubated at 37 ° C for 48 h.
- the evaluation is carried out by reading in the dilution series at which dilution level of the substance to be tested for microbistatic activity the growth of the test germs was suppressed, that is to say the broth or wort remained clear.
- the following table shows the microbistatic activity of the substances of Examples 1 and 2 against gram-positive test organisms (Staphylococcus aureus and Streptococcus mutans) and Gram-negative T estkeimen (Pseudomonas aeruginosa and Escherichia coli).
- the inhibitory concentrations are given in ppm in the table.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863611522 DE3611522A1 (de) | 1986-04-05 | 1986-04-05 | Diphosphonylierte oxonitrille, verfahren zu ihrer herstellung und ihre verwendung in mikrobistatischen zusammensetzungen sowie mikrobistatisch wirksame, diphosphonylierte oxonitrile enthaltende zusammensetzungen |
| DE3611522 | 1986-04-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0240918A1 true EP0240918A1 (fr) | 1987-10-14 |
| EP0240918B1 EP0240918B1 (fr) | 1990-05-02 |
Family
ID=6298064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP87104805A Expired - Lifetime EP0240918B1 (fr) | 1986-04-05 | 1987-03-28 | Oxonitriles diphosphonylés, procédé de leur préparation et leur utilisation en compositions microbistatiques et compositions microbistatiques contenant des oxonitriles diphosphonylés |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4719050A (fr) |
| EP (1) | EP0240918B1 (fr) |
| DE (2) | DE3611522A1 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3724653A1 (de) * | 1987-07-25 | 1989-02-02 | Henkel Kgaa | Olefinische diphosphonsaeuren, verfahren zu ihrer herstellung und ihre verwendung als thresholder sowie komplexierend wirkende, olefinische diphosphonsaeuren enthaltende zusammensetzungen |
| GB9513731D0 (en) * | 1995-07-05 | 1995-09-06 | Procter & Gamble | Bactericidal compositions |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2754821B2 (de) * | 1977-12-09 | 1981-01-08 | Benckiser-Knapsack Gmbh, 6802 Ladenburg | Verfahren zur Herstellung von 1 -Aminoalkan-1,1 -diphosphonsäuren |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US54195A (en) * | 1866-04-24 | Improved machine for soldering tin cans | ||
| DE1002355C2 (de) * | 1954-05-03 | 1957-07-25 | Thomae Gmbh Dr K | Verfahren zur Herstellung von ª‡-prim.-Amino-diphosphonsaeuren und deren Estern |
| DE1958123C3 (de) * | 1969-11-19 | 1978-09-28 | Henkel Kgaa, 4000 Duesseldorf | Verfahren zur Herstellung von 1 -Aminoalkan-1,1 -diphosphonsäuren oder deren Salzen |
| US3899496A (en) * | 1970-10-06 | 1975-08-12 | Henkel & Cie Gmbh | Production of 1-aminoalkane-1,1-diphosphonic acids |
| DE2115737C3 (de) * | 1971-03-31 | 1979-11-08 | Henkel Kgaa, 4000 Duesseldorf | Verfahren zur Herstellung von 1 - Aminoalkan-1,1 -diphosphonsäuren |
| GB1508772A (en) * | 1975-04-04 | 1978-04-26 | Shell Int Research | Biologically active compositions |
| DE2625767C3 (de) * | 1976-06-09 | 1980-06-04 | Benckiser-Knapsack Gmbh, 6802 Ladenburg | Verfahren zur Herstellung von 1-Aminoalkan-1,1 -diphosphonsäuren |
| US4239695A (en) * | 1977-03-24 | 1980-12-16 | Magna Corporation | Method of preparing phosphonates from nitriles |
-
1986
- 1986-04-05 DE DE19863611522 patent/DE3611522A1/de not_active Withdrawn
-
1987
- 1987-03-16 US US07/026,098 patent/US4719050A/en not_active Expired - Fee Related
- 1987-03-28 DE DE8787104805T patent/DE3762517D1/de not_active Expired - Fee Related
- 1987-03-28 EP EP87104805A patent/EP0240918B1/fr not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2754821B2 (de) * | 1977-12-09 | 1981-01-08 | Benckiser-Knapsack Gmbh, 6802 Ladenburg | Verfahren zur Herstellung von 1 -Aminoalkan-1,1 -diphosphonsäuren |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3611522A1 (de) | 1987-10-08 |
| DE3762517D1 (de) | 1990-06-07 |
| EP0240918B1 (fr) | 1990-05-02 |
| US4719050A (en) | 1988-01-12 |
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